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Search Hotels with Pool in Middlesboro

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Check availability on Middlesboro Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Middlesboro hotels with a pool

Property amenity
Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG

Holiday Inn Express Middlesboro by IHG
2.5 star property
Middlesboro
9.6 out of 10, Exceptional, (692)
"Clean hotel, good breakfast options."
United States
Harold
The price is Rp2.028.565
Rp2.236.283 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Middlesboro by IHG
Double Room, Smoking | Desk, blackout curtains, free WiFi, bed sheets
Boone Trail Inn

Boone Trail Inn

Boone Trail Inn
2.0 star property
Middlesboro
7.2 out of 10, Good, (111)
"So the room seemed clean and the owners were vry kind the price was low all in all it was ok for a cheap motel but yall theres roaches i woke up with 1 crawling on the headboard. "
United States
Amy
The price is Rp1.017.016
Rp1.397.987 total
includes taxes & fees
27 Dec - 28 Dec
Boone Trail Inn
Seasonal outdoor pool
Suburban Studios Middlesboro

Suburban Studios Middlesboro

Suburban Studios Middlesboro
2.0 star property
Middlesboro
8.0 out of 10, Very good, (67)
"The newly renovated very clean room was comfortable and clean. All staff were very friendly and we had no issues with our stay. Would stay again when in this area! "
United States
Becky
The price is Rp1.303.287
Rp1.436.744 total
includes taxes & fees
4 Jan - 5 Jan 2026
Suburban Studios Middlesboro
Seasonal outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
Econo Lodge Middlesboro

Econo Lodge Middlesboro

Econo Lodge Middlesboro
2.0 star property
Middlesboro
7.4 out of 10, Good, (445)
"Clean place with friendly staff. "
United States
James
The price is Rp1.494.971
Rp1.648.056 total
includes taxes & fees
28 Dec - 29 Dec
Econo Lodge Middlesboro
Outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers
Pine Mountain State Resort Park

Pine Mountain State Resort Park

Pine Mountain State Resort Park
3.0 star property
Pineville
9.0 out of 10, Wonderful, (672)
"Great place to stay!"
United States
William
The price is Rp1.606.466
Rp1.771.030 total
includes taxes & fees
2 Jan - 3 Jan 2026
Pine Mountain State Resort Park
Front of property
Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line

Days Inn by Wyndham Jellico - Tennessee State Line
2.0 star property
Jellico
7.2 out of 10, Good, (1000)
"Great staff, clean room, upgraded room, recently renovated room, nice Mountain View. "
United States
Ashley
The price is Rp1.238.834
Rp1.415.368 total
includes taxes & fees
4 Jan - 5 Jan 2026
Days Inn by Wyndham Jellico - Tennessee State Line
Indoor pool
Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG

Holiday Inn Express Williamsburg by IHG
2.5 star property
Williamsburg
9.0 out of 10, Wonderful, (1000)
"Staff was nice and breakfast was good"
United States
nicole
The price is Rp1.925.215
Rp2.177.167 total
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Inn Express Williamsburg by IHG
Business centre
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Barbourville
8.2 out of 10, Very good, (267)
"Room was clean and clerk was nice especially since it was early morning "
United States
Billy
The price is Rp1.607.973
Rp1.823.763 total
includes taxes & fees
25 Jan - 26 Jan 2026
Quality Inn
Property grounds
Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club

Woodlake Lodge Golf and Country Club
3.0 star property
Tazewell
9.4 out of 10, Exceptional, (142)
"Gym was closed, restaurant was closed... pool was nice. Course is beautiful."
United States
Daniel
The price is Rp2.176.330
Rp2.443.014 total
includes taxes & fees
1 Jan - 2 Jan 2026
Woodlake Lodge Golf and Country Club
BBQ/picnic Area
Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg

Super 8 by Wyndham Williamsburg
2.5 star property
Williamsburg
5.8 out of 10, (774)
"Price was right room was clean. Many choices to eat. Staff was pleasant. "
United States
Susan
The price is Rp996.090
Rp1.108.648 total
includes taxes & fees
11 Jan - 12 Jan 2026
Super 8 by Wyndham Williamsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlesboro Hotel Reviews

Pine Mountain State Resort Park

Pine Mountain State Resort Park

10/10 Excellent
"All great!"
Henry 1-night trip
Posted 8 days ago
Pine Mountain State Resort Park

Frequently asked questions

What are some accommodation options with pools in Middlesboro?
Sleep Inn & Suites Middlesboro: Offers buffet, an outdoor pool and free self parking. Holiday Inn Express Middlesboro by IHG: Provides continental, a seasonal outdoor pool and free self parking. Econo Lodge Middlesboro: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Boone Trail Inn: Offers daily, an indoor pool and free self parking. Holiday Inn Express Williamsburg by IHG: Features daily, a seasonal outdoor pool and free self parking.
What is there to see and do in Middlesboro?
Spend some time experiencing the great outdoors at Kentucky Ridge State Forest. During your stay, visit sights such as Middlesboro Mall, Cumberland Gap National Historical Park and Bell County Historical Society Museum. Take in the natural beauty of Middlesboro with the mountain views.
When is the best time to book a hotel with a pool in Middlesboro?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Middlesboro in the warmest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 5°C.